Pineland Holiday Rentals
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
58 rentals in Pineland.
Sort by:
Tripadvisor Sort
1 Minute to Beach, Luxury New pool home, Gulf sunrise and sunset Views
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
*** LAST MINUTE SPECIAL ON JANUARY 2ND TO 9TH!!! INQUIRE TODAY!!! ***
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Bluefin Beach House
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Rockstar Beach House North Captiva Island (Accessible by ferry boat only)
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Perfect Distancing Opportunity with Uncrowded Beaches, Hiking, Biking, Kayaking
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Serendipity - Pool, 2 Golf Carts, NCIC, location, location, location!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Oceanfront Luxury Home with Secluded Private Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Beachfront, Pet Friendly Home, Free Cancellation - 202
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
NEW RENTAL*LUXURY HOME*STEPS 2 OCEAN* OVERSIZED POOL*LOCAL OWNERS*LO FEES
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Tropical paradise awaits at the Blue Tortuga
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Pineland rentals sent straight to your email!
Beach's Edge, One Of A Kind Beachfront Experience
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Perfect Placement, Beautiful Ocean Front Home
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Las Olas, 360* Ocean View, close to the best Beach on Island!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Windows on the Water 'W.O.W' A new ocean front oasis! Come enjoy the view!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Hidden Treasure - Secluded NEW Home - Pool-Tiki-Basketball- Near Beach- Club Use
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
New luxury home, 2 min to beach, 360 water views, club amenities
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
Check-in
Check-out
'Sea Urchins' ***** Private Property Beachfront with Beachside Pool & Boat Dock
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Easy Walk to Beautiful Beach, Sleep 10 In Beds, Watch the Sunset From Your Deck
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Newly Renovated Island Pool Home
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
BEAUTY & THE BEACH - LUXE BEACHFRONT MANSION, WEDDINGS, HEATED POOL, BOAT SLIP
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Paradise Found/ North Captiva / Heated Pool
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Island Oasis/Hidden Beach House-Private pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
FLORIDA AT THE BEACH, NEWLY REMODELED 2021- BEACH -OCEAN VIEW- GOLF CART
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
TARPON COVE - Coastal Luxury 2 Bedroom 2 Bathroom Island Home
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Beachfront, Pet Friendly Home, Free Cancellation - 201
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Captiva Beach Sunset ~Gulf front, private pool, 5 BR, NCIC & Airstrip Membership
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Waterfront Property with Dock and 2 Minute Walk to the Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Perfect Beach, Private Pool and Hot tub. Best Beach Sunset Views on the Island.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Remember When, Old Florida Beach House
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
SEA LA VIE- BEACHFRONT-Large & Private, sleeps 10+Club Membership, 2 golf carts
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Under New Management-SMUGGLERS HIDEAWAY-Private Pool-Hot Tub-Club Access-Sleep 7
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Romantic beach cottage with golf cart kayaks and bikes. Remodeled Coastal charm
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Bayfront Beach Escape
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
LAST MINUTE SPECIALS, PRIVATE BEACHES, COME GET AWAY! HEATED POOL & PRIVATE BAR!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Vitamin SEA 365. Off the grid Bliss. Private Beach and Dock
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Steps from the beach, Gulf and Sound Views, Pool and Cabana
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Nice spacious & charming home. Kayak, golf carts , bikes & free wine included.
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
PEACE OF PARADISE - Private Resort Style Pool & Private Beach Access - Sleeps 10
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Near beach, includes golf cart , bikes , kayaks and pool , 5 stars, Boat Slip !
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Second Star is nestled in palms and just 800' to the beach overlooking the lake!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
13 Sunset Captiva 2 Bedroom / 2 Bath House
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
NEW LISTING! SERENITY NOW, SLEEPS 14, 4 KINGS, SCREENED-IN HEATED POOL, CLUB
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Welcome to paradise! You're now on island time!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Luxury private pool home, stunning views, just steps to beach on Captiva Island
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Island Queen, Luxury in Paradise, 200ft to Beach
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Doc Holiday - ‘Old Florida’ Cottage, 600 ft frm beach, Sleeps 8 in beds, pets ok
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Coconut Castaway | New Rental, Newly remodeled, Ocean Views, Hot Tub, Golf Cart
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Cottage Secluded in Palms 2 minute walk to Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Newly Built Floridays, Pool, Beachview, Lots Amenities
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
12
Frequently Asked Questions about Pineland
- Yes, here are some popular holiday rentals in Pineland that have a pool:\n
- \n
- Oceanfront Luxury Home with Secluded Private Beach \n
- Perfect Placement, Beautiful Ocean Front Home \n
- Beach's Edge, One Of A Kind Beachfront Experience \n
- Yes, here are some popular holiday rentals in Pineland that have internet access:\n
- \n
- Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico \n
- Oceanfront Luxury Home with Secluded Private Beach \n
- Perfect Placement, Beautiful Ocean Front Home \n
- The best pet friendly rentals in Pineland are:\n
- \n
- Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico \n
- Oceanfront Luxury Home with Secluded Private Beach \n
- Perfect Placement, Beautiful Ocean Front Home \n
- Some of the most popular kid friendly rentals in Pineland are:\n
- \n
- Spring Warrior Fish Camp Studio Room, Located On the Gulf of Mexico \n
- Oceanfront Luxury Home with Secluded Private Beach \n
- Perfect Placement, Beautiful Ocean Front Home \n